7-Fluoro-4-nitrobenzo-2-oxa-1,3-diazole → 2-Nbdlg

HRID 876095

Reaction equation

HRID 876095 reaction equation
Cl.[OH:2][CH:3]1[O:11][C@@H:10]([CH2:12][OH:13])[C@H:8]([OH:9])[C@@H:6]([OH:7])[C@@H:4]1[NH2:5].C([O-])(O)=O.[Na+].F[C:20]1[C:28]2[C:24](=[N:25][O:26][N:27]=2)[C:23]([N+:29]([O-:31])=[O:30])=[CH:22][CH:21]=1>O.CO>[CH:21]1[CH:22]=[C:23]([N+:29]([O-:31])=[O:30])[C:24]2[C:28](=[N:27][O:26][N:25]=2)[C:20]=1[NH:5][C@@H:4]([C@H:6]([OH:7])[C@@H:8]([OH:9])[C@@H:10]([OH:11])[CH2:12][OH:13])[CH:3]=[O:2]

Participants

6

Reactant 3

HCID 1221237-Fluoro-4-nitrobenzo-2-oxa-1,3-diazoleHCID 516892Sodium BicarbonateHCID 45933886(3S,4S,5R,6S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol;hydrochloride

Product 1

HCID 873081042-Nbdlg

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
37 °C

Procedure

In a brown flask, L-glucosamine hydrochloride (40.0 mg) and NaHCO3 (26.0 mg) were placed and dissolved in water (800 μl). A solution in which 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) (92.0 mg) was dissolved in methanol (4.0 ml) was added thereto, and under an argon atmosphere, the resulting mixture was stirred for 2 hours at a bath temperature of 37° C. Thereafter, the mixture was stirred at room temperature for an additional 40 minutes. Methanol was removed by concentration under reduced pressure, and the resulting precipitates (unnecessary substances derived from NBD-F) were removed by filtration. The precipitates were washed with water, and the filtrate and the washing solution were combined, followed by purification by HPLC. A target fraction was collected and lyophilized, whereby a target product was obtained (yield: 48.7 mg, yield ratio: 76%).

Workup

  1. additionwas added
  2. stirringThereafter, the mixture was stirred at room temperature for an additional 40 minutes
  3. customMethanol was removed by concentration under reduced pressure
  4. customthe resulting precipitates (unnecessary substances derived from NBD-F)
  5. customwere removed by filtration
  6. washThe precipitates were washed with water
  7. customfollowed by purification by HPLC
  8. customA target fraction was collected
  9. customwhereby a target product was obtained
  10. custom(yield: 48.7 mg, yield ratio: 76%)

Sources & evidence

ORD record
ord-f6c1e9a5909b4aae9c96477c7f1ebd69
Source dataset
uspto-grants-2015_03
Patent number
US08986656B2

Linked notes

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